Classifications

• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
  • A61Q5/00—Preparations for care of the hair
  • A61Q5/10—Preparations for permanently dyeing the hair
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
  • A61K8/00—Cosmetics or similar toiletry preparations
  • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
  • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
  • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
  • A61K8/4906—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom
  • A61K8/4926—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom having six membered rings

Definitions

• This invention is directed to oxidation hair dyes. More specifically, this invention is directed to substituted dihydroxypyridines and their use as coupling components in oxidation hair dyes, especially those having tetraaminopyridines as developer components.
• Dyes known as oxidation dyes which are produced by oxidative coupling of a developer component with a coupling component, are preferred due to their intense colors, the mild reaction conditions under which they are formed, and their very good fastness properties.
• Nitrogen bases such as p-phenylenediamine derivatives, diaminopyridines, 4-aminopyrazolone derivatives, and heterocyclic hydrazones are generally used as developer substances. Phenols, m-phenylenediamine derivatives, naphthols, resorcinol derivatives, and pyrazolones are useful as coupling components.
• the search for suitable oxidation hair dyes includes the task of finding the proper components that meet the above-mentioned prerequisites in an optimal fashion.
• the hair dyestuffs are based upon oxidation dyes comprising substituted dihydroxypyridine compounds of the formula ##STR1## wherein R represents an alkyl or hydroxyalkyl having from 1 to 4 carbon atoms and X and Y each represent a hydroxyl group or an alkyl having from 1 to 4 carbon atoms, with the proviso that one of X and Y will represent a hydroxyl group and the other will represent an alkyl, or salts thereof with inorganic or organic acids, as coupling component, and, as developer component, one or more of the conventional developer substances used in oxidation hair dyes.
• Such hair dyestuffs can meet the above-mentioned requirements to an especially high degree and consequently represent especially valuable combinations in the area of oxidation hair dyes.
• the dihydroxypyridines to be used as coupling components according to the invention are themselves well-known compounds and can be prepared by methods known from the literature. For example, the preparation of 2,6-dihydroxy-3,4-dimethylpyridine as well as 2,4-dihydroxy-5,6-dimethylpyridine was described in Rec. Trav. Chim. 63: 231, 1944, the preparation of 2,6-dihydroxy-3-ethyl-4-methylpyridine in Helv. Chim. Acta 2: 338, 1981, and the preparation of 2,6-dihydroxy-3- ⁇ -hydroxyethyl-4-methylpyridine in Austral. J. Chem. 9: 244, 1956.
• the use of the dihydroxypyridines according to the invention as component in hair dye products is new and cannot be deduced from publications of the state of the art.
• the compounds according to the invention Upon the use of the compounds according to the invention, that is, the substituted dihydroxypyridine compounds of Formula I and the salts thereof, as coupling components together with developers generally used for oxidation hair dyes, the resulting hair dyes yield very intense shades in the yellow to blue-brown range, and thus such use represents a considerable expansion of the possibilities in oxidation hair dyeing.
• the compounds according to the invention are characterized by very good fastness characteristics of the resulting colors, good solubility in water, good shelf-life, and toxicological as well as dermatological safety.
• R represents a methyl, ethyl, or 2-hydroxyethyl group and one of X and Y represents a hydroxyl group and the other of X and Y represents a methyl group.
• R 1 to R 6 may each be a hydrogen atom; an alkyl moiety with from 1 to 4 carbon atoms; or the redical --(CH 2 ) n X in which n is an integer of from 1 to 4 and X is selected from the group consisting of a hydroxyl group, a halogen atom, and --NR 7 R 8 in which R 7 and R 8 are each a hydrogen atom or an alkyl group having from 1 to 4 carbon atoms or together with the nitrogen atom R 7 and R 8 form a 5- or 6-membered heterocyclic ring of carbon atoms and the nitrogen atom, optionally containing an additional nitrogen or oxygen atom in the ring in place of a carbon atom, or each of R 1 and R 2 , R
• the compounds 2,4,5,6-tetraaminopyrimidine and its derivatives are known as developer components in hair dyes from U.S. Pat. No. Re. 30,199, incorporated herein by reference.
• the dihydroxypyridines according to the invention are valuable yellow coupling substances in hair dye products using this type of developer.
• the dihydroxypyridines to be used according to the invention are used simultaneously with 2,4,5,6-tetraaminopyrimidine or derivatives thereof as developer and 2-chloro-6-methyl-3-aminophenol as blue coupling agent in hair dye products.
• 2-Chloro-6-methyl-3-aminophenol is a very valuable blue coupling agent in hair dye products based upon 2,4,5,6-tetraaminopyridmidines as developer.
• a known yellow coupling agent for this system for example, 2,7-dihydroxynaphthalene, 6-hydroxyquinoline, or 8-amino-6-methoxyquinoline, the colors obtained are mainly of a bluish hue.
• substituted dihydroxypyridines of Formula I to be used as coupling components according to the invention can be used either as such or in the form of their salts with inorganic or organic acids, for example, as chlorides, sulfates, phosphates, acetates, propionates, lactates, or citrates.
• substituted dihydroxypyridines to be used according to the invention can also be used together with additional, known coupling components in hair dye products.
• known coupling agents include resorcinol, 2-methylresorcinol, 4-chlororesorcinol, and 2,4-dichloro-3-aminophenol.
• the developer components to be used according to the invention are those that are conventionally used in oxidatively coupled dyestuffs, including the aforementioned compounds of Formula II.
• developer components include primary aromatic amines with an additional functional group in the p-position, such as p-phenylenediamine, p-toluylenediamine, p-aminophenol, N-methyl-p-phenylenediamine, N,N-dimethyl-p-phenylenediamine, N,N-diethyl-2-methyl-p-phenylenediamine, N-ethyl-N-hydroxyethyl-p-phenylenediamine, chloro-p-phenylenediamine, N,N-bis-hydroxyethylamino-p-phenylenediamine, methoxy-p-phenylenediamine, 2,5-diaminoanisole, 2,6-dichloro-p-phenylenediamine, 2-chloro-6-bromo-
• Diaminopyridine derivatives such as 1-methyl-pyrrolidon-(2)-hydrazone
• 4-amino-pyrazolone derivatives such as 4-amino-1-phenyl-3-carbamoylpyrazolone-5
• N-butyl-N-sulfobutyl-p-phenylenediamine are additional examples of useful developer components.
• Examples of the above-mentioned developer type of the tetraaminopyrimidines of Formula II, which also can be used as such or in the form of their salts with inorganic or organic acids, for example, as chlorides, sulfates, phosphates, acetates, propionates, lactates, or citrates, and which are advantageously used together with substituted dihydroxypyridines of Formula I in hair dye products, include the following:
• the coupling and developer components generally are used in approximately equimolar amounts. Although the equimolar use proves suitable, it is not disadvantageous to add the coupling component in a certain excess or deficiency.
• the coupling and developer components can be present in a molar range of from about 2:1 to 1:2, a 10% or less excess or deficiency being preferred.
• the developer component and the coupling substance are homogeneous or pure products.
• the developer component may consist of mixtures of the developer compounds to be used according to the invention, and the coupling substance may be in the form of mixtures of substituted dihydroxypyridines or salts thereof according to the invention.
• the hair dyestuffs according to the invention may also contain, if desired, conventional, directly applicable dyes in the mixture, provided that such are necessary for the creation of certain color nuances.
• the oxidative coupling that is, the development of the dye, can in principle be carried out with atmospheric oxygen as is done with other oxidation hair dyestuffs also.
• chemical oxidation agents are advantageously employed.
• Particularly suitable as such oxidation agents are hydrogen peroxide or its addition compounds with urea, melamine, or sodium borate as well as mixtures of such hydrogen peroxide adducts with potassium peroxydisulfate.
• the tetraaminopyrimidines offer the advantage as developer component that they yield completely satisfactory dye results even with oxidative coupling by atmospheric oxygen, and that damage to the hair due to oxidation agents used otherwise for the oxidative coupling is consequently prevented. If, however, a lightening effect on the hair is desired together with the dye, the simultaneous use of oxidation agents is necessary.
• the hair dyes according to the invention are incorporated into respective cosmetic preparations such as creams, emulsions, gels, or also simple solutions for their use and are mixed with one of the mentioned oxidation agents immediately before application to the hair.
• concentration of the coupling/developer combination in such dyes is from about 0.2 to 5 percent by weight, preferably from about 1 to 3 percent by weight, based on the total weight of the preparation.
• the dye components are mixed with the other components normally used in such preparations.
• additional components include, for example, wetting or emulsifying agents of the anionic or nonionic type such as alkylbenzenesulfonates, sulfates of fatty alcohols, higher alkylsulfonates, alkanolamides of fatty acids adducts of ethylene oxide onto fatty alcohols, thickeners such as methyl cellulose, starch, higher fatty alcohols, paraffin oil, and fatty acids, and perfume oils and hair-conditioning and grooming agents such as pantothenic acid and cholesterol.
• wetting or emulsifying agents of the anionic or nonionic type such as alkylbenzenesulfonates, sulfates of fatty alcohols, higher alkylsulfonates, alkanolamides of fatty acids adducts of ethylene oxide onto fatty alcohols, thickeners such as methyl cellulose, starch, higher fatty alcohols, paraffin
• wetting and emulsifying agents can be present in concentrations of from about 0.5 to 30 percent by weight, preferably from about 1 to 15 percent by weight, and thickeners can be present in concentrations of from about 0.1 to 25 percent by weight, preferably from about 1 to 15 percent by weight, based, respectively, on the weight of the total preparation.
• a hair dye according to the invention can be applied in a weakly acid, neutral or particularly alkaline medium at a pH of 8 to 10, regardless of whether it is in the form of a solution, an emulsion, a cream, or a gel.
• the application temperatures range from about 15° to 40° C., preferably at room temperature.
• the preparation is removed by rinsing from the dyed hair.
• the hair is washed with a mild shampoo and dried.
• the hair which can be any color or length, can be either "live" hair or hair that has been cut, such as that in a wig.
• the colors that can be achieved with the hair dyes according to the invention cover a broad spectrum of yellow to blue-brown shades, with the use of various developer and coupling components.
• the colors obtained show good fastness to light, shampooing, and abrasion, and they are easily stripped with reducing agents.
• E-13 2-morpholino-4,5,6-triaminopyrimidine.
• the hair dyes according to the invention were used in the form of a cream emulsion. For this, 0.01 mol of each of the developer substances and coupling substances listed in the table below were worked into an emulsion containing
• the pH of the emulsion was adjusted to 9.5 with ammonia, and the emulsion was made up to 100 parts by weight with water.
• Oxidative coupling was carried out with a 3% hydrogen peroxide solution acting as oxidation agent, 10 parts by weight of the hydrogen peroxide solution being added to 100 parts by weight of the emulsion.
• the particular dyeing cream was applied to standardized human hair which was 90% grey and which had not been specially pretreated, and the cream was left on the hair for 30 minutes at room temperature. After completion of the dyeing process, the hair was washed out with a conventional commercial shampoo and dried.
• the colorations obtained by this process are complied in the table below:
• K-7 8-amino-6-methoxyquinoline.

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• Health & Medical Sciences (AREA)
• Life Sciences & Earth Sciences (AREA)
• Animal Behavior & Ethology (AREA)
• General Health & Medical Sciences (AREA)
• Public Health (AREA)
• Veterinary Medicine (AREA)
• Birds (AREA)
• Epidemiology (AREA)
• Cosmetics (AREA)
• Pyridine Compounds (AREA)
• Agricultural Chemicals And Associated Chemicals (AREA)
• Photoreceptors In Electrophotography (AREA)
• Investigating Or Analyzing Non-Biological Materials By The Use Of Chemical Means (AREA)

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Cited By (9)

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• 1981
  • 1981-04-18 DE DE19813115643 patent/DE3115643A1/de not_active Withdrawn
• 1982
  • 1982-03-22 DK DK128282A patent/DK148897C/da not_active IP Right Cessation
  • 1982-03-22 NO NO820938A patent/NO159340C/no unknown
  • 1982-03-22 FI FI820988A patent/FI72871C/fi not_active IP Right Cessation
  • 1982-04-10 EP EP82103092A patent/EP0063736B1/fr not_active Expired
  • 1982-04-10 AT AT82103092T patent/ATE17314T1/de not_active IP Right Cessation
  • 1982-04-10 DE DE8282103092T patent/DE3268365D1/de not_active Expired
  • 1982-04-16 JP JP57062616A patent/JPS57183710A/ja active Granted
• 1987
  • 1987-06-24 US US07/065,142 patent/US4838893A/en not_active Expired - Lifetime

Patent Citations (3)

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